3-[[N-(2,6-diethylphenyl)carbamoyl]methyl]thymidine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3-[[N-(2,6-diethylphenyl)carbamoyl]methyl]thymidine
• 英文别名: N-(2,6-diethylphenyl)-2-[3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]acetamide
• 化学式: C₂₂H₂₉N₃O₆
• 分子量: 431.489
• InChiKey: CEHAOFWJVZHXAY-YQVWRLOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,6-二乙基苯胺 在 sodium acetate buffer 、 nuclease P₁ 、 碳酸氢钠 、 zinc(II) chloride 作用下， 以 乙二醇甲醚 、 水 、 乙酸乙酯 为溶剂， 反应 28.0h， 生成 3-[[N-(2,6-diethylphenyl)carbamoyl]methyl]thymidine
  参考文献：
  名称：

  Synthesis and Characterization of Adducts of Alachlor and 2-Chloro-N-(2,6-diethylphenyl)acetamide with 2'-Deoxyguanosine, Thymidine, and Their 3'-Monophosphates

  摘要：

  Adducts of the preemergence herbicide 2-chloro-N-(methoxymethyl)-N-(2,6-diethylphenyl)acetamide (alachlor) and 2-chloro-N-(2,6-diethylphenyl)acetamide (CDEPA) with 2'-deoxyguanosine, thymidine, 2'-deoxyguanosine 3'-monophosphate, and thymidine 3'-monophosphate have been synthesized and characterized. Under mildly basic conditions alachlor and CDEPA form N-1 adducts with 2'-deoxyguanosine and N-3 adducts with thymidine as a result of chlorine displacement. In addition, alachlor formed an N-7 adduct with 2'-deoxyguanosine, 7-[[(N-(methoxymethyl)-N-(2,6-diethylphenyl)carbamoyl]methyl]guanine. N-1 adducts of alachlor and CDEPA with 2'-deoxyguanosine 3'-monophosphate and N-3 adducts with thymidine 3'-monophosphate are also described. In addition to spectroscopic data, structural proof included the dephosphorylation of each nucleotide adduct to its corresponding nucleoside adduct by nuclease P1. Alachlor and alachlor adducts but not CDEPA and CDEPA adducts exhibited rotational isomerism as evidenced by proton and C-13 NMR studies. These rotamers were attributed to hindered rotation about the shortened N-carbonyl bond. Computational methods employing molecular mechanics and quantum mechanics were used to characterize the structures and energies of these rotamers to account for the patterns of duplicate NMR resonances observed.

  DOI：

  10.1021/tx00044a005

文献信息

• Synthesis and Characterization of Adducts of Alachlor and 2-Chloro-N-(2,6-diethylphenyl)acetamide with 2'-Deoxyguanosine, Thymidine, and Their 3'-Monophosphates
  作者：Stephen Nesnow、Satish C. Agarwal、William T. Padgett、Guy R. Lambert、Phillip Boone、Ann M. Richard

  DOI：10.1021/tx00044a005

  日期：1995.3

  Adducts of the preemergence herbicide 2-chloro-N-(methoxymethyl)-N-(2,6-diethylphenyl)acetamide (alachlor) and 2-chloro-N-(2,6-diethylphenyl)acetamide (CDEPA) with 2'-deoxyguanosine, thymidine, 2'-deoxyguanosine 3'-monophosphate, and thymidine 3'-monophosphate have been synthesized and characterized. Under mildly basic conditions alachlor and CDEPA form N-1 adducts with 2'-deoxyguanosine and N-3 adducts with thymidine as a result of chlorine displacement. In addition, alachlor formed an N-7 adduct with 2'-deoxyguanosine, 7-[[(N-(methoxymethyl)-N-(2,6-diethylphenyl)carbamoyl]methyl]guanine. N-1 adducts of alachlor and CDEPA with 2'-deoxyguanosine 3'-monophosphate and N-3 adducts with thymidine 3'-monophosphate are also described. In addition to spectroscopic data, structural proof included the dephosphorylation of each nucleotide adduct to its corresponding nucleoside adduct by nuclease P1. Alachlor and alachlor adducts but not CDEPA and CDEPA adducts exhibited rotational isomerism as evidenced by proton and C-13 NMR studies. These rotamers were attributed to hindered rotation about the shortened N-carbonyl bond. Computational methods employing molecular mechanics and quantum mechanics were used to characterize the structures and energies of these rotamers to account for the patterns of duplicate NMR resonances observed.